PROTECTION OF HYDROXYL IN THE SYNTHESIS OF SEMISYNTHETIC β-LACTAM ANTIBIOTICS

The 2-methoxypropan-2-yl group fulfills the need of a hydroxyl protecting group generally suitable for the synthesis of β-lactam antibiotics, satisfying the criteria of low-cost, convenience and selectivity in formation, and, above all, ease of deprotection under conditions compatible to the highly...

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Bibliographic Details
Published inJournal of antibiotics Vol. 34; no. 9; pp. 1157 - 1163
Main Author WOO, PETER W. K.
Format Journal Article
LanguageEnglish
Published Japan JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1981
Subjects
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
Pseudomonas aeruginosa
Pseudomonas aeruginosa - drug effects
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Summary:The 2-methoxypropan-2-yl group fulfills the need of a hydroxyl protecting group generally suitable for the synthesis of β-lactam antibiotics, satisfying the criteria of low-cost, convenience and selectivity in formation, and, above all, ease of deprotection under conditions compatible to the highly sensitive β-lactam function and without contamination of the final products. The use of this protecting group has enabled the successful attachment of 6-[4-(N-acetyl-4-hydroxyl-L-prolylamino)phenyl]-1, 2-dihydro-2-oxo-3-pyridinecarboxyl group, through an amide linkage, to amoxicillin, cephaloglycin, and the 3-[[(1-carboxymethyl)-1-H-tetrazol-5-yl]thio]methyl analogue of the latter, yielding broad-spectrum antibiotics with notably good activities against strains of Pseudomonas aeruginosa.
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ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.34.1157